Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(5): 807-810
DOI: 10.1055/s-0029-1218603
DOI: 10.1055/s-0029-1218603
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereospecific Total Synthesis of (+)-Davana Acid, (+)-Nordavanone and (+)-Davanone
Further Information
Received
4 November 2009
Publication Date:
11 December 2009 (online)
Publication History
Publication Date:
11 December 2009 (online)
Abstract
A short, total synthesis of (+)-davana acid, (+)-nordavanone and (+)-davanone, which are principle components of davana oil, is described. The notable features are the use of the Evans syn aldol reaction and cyclic ether formation by an intramolecular SN2 displacement reaction as key steps.
Key words
Evans aldol - cyclic ether - (-)-linalool - natural product - davana oil
-
1a
Misra LN.Chandra A.Thaken RS. Phytochemistry 1991, 30: 549 -
1b
Thomas AF.Ozainne M. Helv. Chim. Acta 1974, 57: 2062 -
1c
Sipma G.van der Wal B. Recl. Trav. Chim. Pays-Bas 1968, 87: 715 - 2
Hethelye E.Tetenyi P.Kettenes van der Bosh J.Salemink C.Heerma W.Verluis C.Kloosterman J.Sipma G. Phytochemistry 1981, 20: 1847 - 3
Thomas AF.Thommen W.Willhalm B.Hagaman EW.Wenkert E. Helv. Chim. Acta 1974, 57: 2055 - 4
Husain A.Virmani OP.Sharma A.Kumar A.Misra LN. Major Essential Oil-Bearing Plants in India CIMAP; Lucknow: 1988. p.167-181 -
5a
Thomas AF.Pitton G. Helv. Chim. Acta 1971, 1890 -
5b
Baslas RK. Flavour Ind. 1971, 2: 370 - 6
Vajs V.Trifunovic S.Janackovic P.Sokovic M.Milosavljevic S.Tesevic V. J. Serb. Chem. Soc. 2004, 69: 969 - 7
Perfumi M.Paparelli F.Cingolani M. J. Essent. Oil Res. 1995, 7: 387 -
8a
Molander GA.Hass J. Tetrahedron 1999, 55: 617 -
8b
Birch AJ.Corrie JET.Rao GSRS. Aust. J. Chem. 1970, 23: 1811 -
8c
Naegeli P.Weber G. Tetrahedron Lett. 1970, 959 -
9a
Honda Y.Ori A.Tsuchihashi G.-I. Chem. Lett. 1987, 1259 -
9b
Bartlett PA.Holmes CP. Tetrahedron Lett. 1983, 24: 1365 - 10
Morrison KC.Litz JP.Scherpelz KP.Dossa D.Vosburg DA. Org. Lett. 2009, 11: 2217 - 11
Sharpless KB.Amberg W.Bennani YL.Crispino GA.Hartung J.Jeong K.-S.Kwong H.-L.Morikawa K.Wang Z.-M.Xu D.-Q.Zhang X.-L. J. Org. Chem. 1992, 57: 2768 - 12
Evans DA.Bartoli J.Shih TL. J. Am. Chem. Soc. 1981, 103: 2127 - 13
Hong B.-C.Hong J.-H.Tsai Y.-C. Angew. Chem. Int. Ed. 1998, 4: 37